JPH0422945A - Silver halide color photographic sensitive material - Google Patents

Abstract

PURPOSE:To obtain the photographic sensitive material which has excellent color developability and high solubility in low and high boiling point solvents and exhibits excellent dispersion stability in these solvents by incorporating a specific 2 equiv. yellow coupler into silver halide emulsion layers. CONSTITUTION:This photosensitive material contains the 2 equiv. yellow coupler expressed by formula I in at least one layer of the silver halide emulsion layers on a substrate. In the formula, Y denotes the residual group of the 2 equiv. yellow coupler contg. the group expressed by -(J-R1)m-O-R2(O-R2-(O-R3)n-(R4)q-X- R5. R1 to R4 respectively denote an alkylene group or arylene group. R5 denotes a hydrogen atom, alkyl group, cycloalkyl group,; (m) and (q) denote 0 or 1; (n) denotes 2 to 10 integer; J and X denote a bivalent combination group con nected by a hetero atom. The silver halide color photographic sensitive material contg. the 2 equiv. yellow coupler which has excellent color developability and high solubility in the low boiling point solvent and exhibits excellent disper sion stability in the solvent is obtd. in this way.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a silver halide color photographic light-sensitive material, and more specifically, it has excellent color development properties, excellent image storage stability, and has a low boiling point used for dispersing couplers. and a novel 2 that has high solubility in high-boiling point solvents and excellent dispersion stability.
This invention relates to a silver halide color photographic light-sensitive material using an equivalent yellow coupler in a silver halide emulsion layer.

[Background of the invention]

In recent years, silver halide color photographic materials (hereinafter simply referred to as color photographic materials) have been developed using developing agents instead of conventional 4-equivalent couplers that require 4 atoms of silver to form one molecule of dye. By introducing an appropriate substituent into the cambling position (active site) of the coupler that reacts with the oxide of
There is a tendency for two-equivalent couplers that require only atoms to be used frequently.

Among such 2-equivalent couplers, active site substituents employed in yellow couplers include those described in, for example, JP-A-50-87650 and U.S. Pat. No. 3,408.
．． Aryloxy group described in specification No. 194, JP-A-51
Oxacylyloxy group as described in JP-A-131325, chroman-4-oxy group as described in JP-A-51-139333, tetrazolyloxy group as described in JP-A-52-43426, 5- as described in JP-A-52-150631 Pyrazolyloxy group, nitrogen-containing heterocyclic group described in Japanese Patent Publication No. 52-115219, urazole group described in Japanese Patent Publication No. 51-33410, hydantoin group described in Japanese Patent Publication No. 51-10783, and U.S. Patent No. 3.227.554 As described in the specification, ruthio groups and the like are known, and some of these have already been put to practical use.

However, with the progress of color photosensitive materials, requirements for couplers are becoming increasingly strict, and further improvements in color development are required. For this reason, various efforts have been made to design coupler molecules. For example, it has been proposed to introduce an alkoxycarbonyl group or an alkylsulfonamide group into the ballast component to improve color development, but this has not been sufficiently improved. do not have.

JP-A-55-142340 describes a 2-equivalent yellow coupler containing one or two ether bonds in the ballast group. Although the coupler described in this publication is intended to have improved color development due to the ether bond in the ballast group, it is no longer sufficient to meet the recent demands for high color development.

Further, there is a growing demand for further improvements not only in color development but also in image storage stability, solubility in low boiling point solvents, and dispersion stability.

Many of the couplers mentioned above, which aim to improve color development, have poor solubility in low-boiling point solvents such as ethyl acetate and high-boiling point solvents such as dibutyl phthalate, so a large amount of solvent must be used to disperse them. However, this method causes inconvenience in the production of color photosensitive materials, and furthermore, it has the disadvantage that it tends to cause precipitation after it is once dispersed in the solvent.

It has become clear that these drawbacks are greatly accentuated under the conditions for thinning the film, which has been strongly sought after in recent years, and become a major obstacle to practical application.

[Purpose of the invention]

The present invention has been made in view of the above problems, and a first object of the present invention is to provide a silver halide color photographic light-sensitive material containing a novel 2-equivalent yellow coupler with excellent color development.

A second object of the present invention is to provide novel 2-equivalent yellow couplers containing halogens that are highly soluble in the low-boiling and high-boiling solvents used to disperse the couplers and exhibit excellent dispersion stability in those solvents. An object of the present invention is to provide a silver oxide color photographic material.

[Structure of the invention]

The above object of the present invention is to provide a silver halide color photographic light-sensitive material having at least one silver halide emulsion layer on a support.
This is achieved by a silver halide color photographic light-sensitive material characterized in that 'i contains a 2-equivalent yellow coupler represented by the following general formula [I].

General formula (1) %Formula% (In the formula, Y is -(J-(JE0-Rz-O-R3)
Represents a 2-equivalent yellow coupler residue containing the group ri-(R4)q-X-R8. R+, Rz,
R* and R4 each represent an alkylene group or an arylene group.

R5 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group. m and q represent 0 or 1, n represents an integer from 2 to 10, and J and X represent a divalent linking group connected via a heteroatom.

[Detailed description of the invention]

In the above general formula (I), R+, Rz, R:l,
The alkylene group and arylene group represented by R4 and R4 are a linear or branched alkylene group having 1 to 25 carbon atoms (for example, methylene, propylene, butylene group, etc.) or an arylene group having 6 to 10 carbon atoms ( Examples include phenylene, naphthylene groups, etc.). The alkylene group and arylene group represented by R1, R2゜R3, and R4 can further have a substituent, and examples of the substituent include, for example, a halogen atom (
For example, chlorine atom, bromine atom, etc.), cyano group, nitro group,
Alkyl groups (e.g. methyl, i-propyl, t-butyl, n-dodecyl, etc.), cycloalkyl groups (e.g. cyclopropyl, cyclohexyl, etc.), aryl groups (e.g. phenyl, p-t- octylphenyl group, 2,4-di-t-amylphenyl group, etc.), hydroxy group, alkoxy group (e.g., methoxy group, 2-ethoxyethoxy group, etc.), aryloxy group (e.g., phenoxy group, 2,4-di- t-amylphenoxy group, 4-(4
-hydroxyphenylsulfonyl) phenoxy group, etc.), heterocyclic oxy group (e.g. 4-pyridyloxy group, 2-hexahydropyranyloxy group, etc.), carbonyloxy group (
For example, alkylcarbonyloxy groups such as acetyloxy group and pivaloyloxy group, aryloxy group such as hendiyloxy group, etc.), sulfonyloxy group (e.g. methanesulfonyloxy group, trifluoromethanesulfonyloxy group, n-dodecanesulfonyloxy group, etc.) Alkylsulfonyloxy group, Hensensulfonyloxy group, p
-) arylsulfonyloxy groups such as luenesulfonyloxy groups), acyl groups (e.g. acetyl groups, alkylcarbonyl groups such as pivaloyl groups, benzoyl groups, 3,5-
arylcarbonyl groups such as di-t-butyl-4-hydroxybenzoyl group), oxycarbonyl groups (e.g. alkoxycarbonyl groups such as methoxycarbonyl group, cyclohexyloxycarbonyl group, n-dodecyloxycarbonyl group, phenoxycarbonyl group) ,2,4-Gt
Aryloxycarbonyl groups such as amylphenoxycarbonyl group, 1-naphthyloxycarbonyl group, and 2
-heterocyclic oxycarbonyl groups such as -pyridyloquinecarbonyl group, 1-phenylpyrazolyl-5-oxycarbonyl group, etc.), alkylcarbamoyl groups such as carbacarbonyl group, arylcarbamoyl groups such as phenylcarbamoyl group, -naphthylcarbamoyl group, etc. ), sulfonyl groups (e.g. alkylsulfonyl groups such as methanesulfonyl group, trifluoromethanesulfonyl group, and arylsulfonyl groups such as p-toluenesulfonyl group), sulfamoyl groups (e.g. dimethylsulfamoyl group, 4-(2
, 4-di-t-amylphenoxy)butylaminosulfonyl group, alkylsulfamoyl group such as phenylsulfamoyl group), amino group (e.g. dimethylamino group, cyclohexylamino group,
alkylamino groups such as n-dodecylamino groups, arylamino groups such as anilino groups and pt-octylanilino groups), sulfonylamino groups (e.g. methanesulfonylamino groups, heptafluoropropanesulfonylamino groups,
Alkylsulfonylamino groups such as n-hexadecylsulfonylamino groups, p-toluenesulfonyl groups, arylsulfonylamino groups such as pentafluorobenzenesulfonylamino), acylamino groups (alkylcarbonylamino groups such as acetylamino groups, myristoylamino groups, etc.) , benzoylamino group, etc.), alkylthio groups (e.g., methylthio group, t-octylthio group, etc.), arylthio groups (e.g., phenylthio group, etc.), and heterocyclic thio groups (e.g., 1-phenyltetrazole-5-thio group). , 5-methyl-1,3,4-oxadiazole-2-thio group, etc.).

The alkyl group represented by R7 in the above general formula (1) is a linear or branched alkyl group having 1 to 25 carbon atoms (e.g. methyl group, i-propyl group, t-butyl group, 2-ethylhexyl group). , n-dodecyl group, 2-hexyldecyl group, etc.). Examples of the cycloalkyl group represented by R5 in the above general formula (1) include cycloalkyl groups having 3 to 8 carbon atoms (eg, cyclopropyl group, cyclohexyl group, etc.). Further, the aryl group represented by R5 in the above general formula (1) includes an aryl group having 6 to 10 carbon atoms (eg, phenyl group, 1-naphthyl group, etc.). The alkyl group, cycloalkyl group, and aryl group represented by R1 can further have a substituent, and examples of the substituent include R+, Rz, R3, and R4 in the above general formula (1).
The substituents having the same meaning as the substituents that can be substituted on the alkyl group, cycloalkyl group, and aryl group represented by these can be mentioned.

In the above general formula (I), m and q represent 0 or 1,
n represents an integer from 2 to 10.

In the above general 2N), J and X are divalent linking groups connected via a heteroatom, such as O 2 and the like. (Here, R4 represents a hydrogen atom, an alkyl group, or an atomyl group.) In the above general formula (1), Y represents a 2-equivalent yellow coupler residue. Preferably, Rlt is a 2-equivalent yellow coupler residue represented by the following general formula [I[]. alkylcarbonyl groups such as, arylcarbonyl groups such as benzoyl group) or general formula (A)
Represents a 5-membered nitrogen-containing heterocyclic group represented by: R'12 where Wl is -N--0-1 and -5O).

(Here, R2□ represents a hydrogen atom or an alkyl group, and r represents an integer from O to 2.) Z is 1,
Represents 2-phenylene, vinylene, or dimethylene.

R11 is a substituent, and in the above general formula [1], RI
+ an alkyl group represented by Rz, R3, and R4,
It is a substituent having the same meaning as a substituent that can be substituted for a cycloalkyl group and an aryl group.

As Rlt, an acyl group is preferable, and a t-butyl group or a p-methoxybenzoyl group is particularly preferable.

In the above general formula [■], Rlt represents the above general formula (1)
represents an aryl group having the same meaning as the aryl group represented by R6. The aryl group represented by RIz may further have a substituent, and examples of the substituent include the above general formula (J
) in Rr, Rz, Rs.

and an alkyl group or cycloalkyl group represented by R4,
and substituents having the same meanings as substituents that can be substituted for the aryl group.

In the above general formula (II), X represents a group that can be separated upon coupling with an oxidized form of a developing agent, and represents, for example, a group represented by the following general formula CB), (C), or CD).

General formula CB) ORs+ R811 represents a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group.

General formula (C) 0CRsz R3□ represents a group having the same meaning as R3□.

Z2 represents a group of nonmetallic atoms necessary to form a 5- to 6-membered ring in cooperation with the nitrogen atom. Here, the atomic groups necessary to form the nonmetallic atomic group include, for example, methylene, methine, substituted methine, R3; c=o, -N- (R33 is a hydrogen atom, an alkyl group, an aryl group, or (represents a heterocyclic group), -N=0
-1 and -5O)u- (u represents an integer from 0 to 2), and the like.

Preferably, X represents a group represented by the following general formulas (E) to (M).

Oxycarbonyl groups such as methoxycarbonyl group or i-propyloxycarbonyl group, acyl group such as acetyl group or benzoyl group, sulfonyl group such as trifluoromethanesulfonyl group or 4-hydroxyphenylsulfonyl group, nitro group, cyano group, halogen atom ,
represents a sulfamoyl group such as a dimethylsulfamoyl group, an acylamino group such as an acetylamino group or a pentafluorobenzoyl group, a sulfonylamino group such as a methanesulfonylamino group), or a hydroxy group, and S represents an integer from 1 to 5. When S is 2 or more, R41 may be the same or different.

R4□ represents a substituent having the same meaning as R41 in the above general formula (E), and [ represents an integer from 1 to 5.

When t is 2 or more, R4□ may be the same or different.

General formula [G] General formula (H) General formula (J) Ra2,
R3 and Ra4 are each a hydrogen atom or a group that can be substituted on these azole rings, specifically, in the alkyl group, cycloalkyl group, and aryl group represented by R1, RLR3+, and R4 in the above general formula CI). Substituents having the same meaning as substitutable substituents are mentioned. R4,
and R44 may be the same or different, and may mutually form a ring.

General formula (K) General formula (L) AS Z 31+ Z! ! is -N--0-1 and -5O)
v (where 1, R4S represents a hydrogen atom, an aryl group or an alkyl group, ■ represents an integer from 0 to 2) -Rab, R41R4g represents the same group as the above R4ff and R44, R4, For example, an alkyl group such as a methyl group or an i-propyl group, a cycloalkyl group, an aryl group such as a phenyl group or a 2,4-di-1-amylphenyl group, an acyl group such as a pivaloyl group or a benzoyl group, a trifluoromethanesulfonyl group Alternatively, it represents a sulfonyl group such as p-)luenesulfonyl group.

R1゜ Y is -N- −N= 10- -SO).

Represents a group of nonmetallic atoms necessary to form a 5- to 6-membered ring. Here, examples of the atomic group necessary to form the nonmetallic atomic group include the groups having the same meaning as 22 described above.

R5O has the same meaning as R3ff, and R5I to R53 have the same meaning as R43 or R44. Furthermore, R3° to R53 may form a ring together with a portion of Z33.

In the general formula (1), -(J-Ra)--0-Rz-O-R3), 1-(
R4) The group represented by q-X-Rs has the above general formula (II)
In R1,.

It may be bonded to any group among R1□ or X, more preferably bonded to R1□ or X, and further preferably bonded to Rlm.

The 2-equivalent yellow coupler represented by the general formula (I) may be bonded at any substituent to form a bis form.

Next, typical examples of the 2-equivalent yellow coupler represented by the general formula [I] used in the present invention will be shown, but the present invention is not limited thereto.

The yellow coupler of the present invention represented by general formula CI) can be easily synthesized by conventionally known methods. Typical synthesis examples of the present invention are shown below.

Synthesis example: Synthesis of exemplary coupler (2) CI C0CHC&H+z (1) Synthesis of 4-equivalent coupler (C) 26.9 g of α-pivaloyl-2-chloro-5-aminoacetanilide (A) was dissolved in 200 ml of ethyl acetate, and water 150m7! and 5.8 g of sodium carbonate were added and stirred vigorously. Add 48.9 g of acid chloride (B) to 150 m7 of ethyl acetate! was added dropwise. (
In addition, acid chloride (B) is disclosed in U.S. Patent No. 4.892.80.
It was synthesized according to the method described in the specification of No. 5. ) After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour, and the organic layer was washed with a 5% aqueous potassium carbonate solution and diluted hydrochloric acid. After dehydration over magnesium sulfate, the solvent was removed under reduced pressure to obtain the desired 4-equivalent coupler (C) as a yellow viscous oil. Yield 66.4g (
98%).

(2) Synthesis of Exemplary Coupler (2) 6.8 g of the 4-equivalent coupler (C) obtained above was dissolved in chloroform 5Q+wji, and 1.4 g of sulfuryl chloride was added dropwise to the solution while cooling with water. After dropping, the water bath was removed and the mixture was stirred for 1 hour. The reaction solution was washed with water, dehydrated with magnesium sulfate, and the solvent was removed under reduced pressure.

The obtained residue was dissolved in 50 tsl of acetone, 3.0 g of 3-butyl-4-phenylurazole and 1.8 g of potassium carbonate were added thereto, and the mixture was heated under reflux for 3 hours. After filtering out insoluble matter, the mixture was washed with 5% aqueous potassium carbonate solution and diluted hydrochloric acid. After dehydration with magnesium sulfate, the solvent was removed under reduced pressure.

The obtained residue was dissolved in 50 nl of methanol, 0.5 g of sodium hydroxide was added thereto, and the mixture was stirred at room temperature for 1 hour. After neutralizing with 2N hydrochloric acid, the solvent was removed under reduced pressure, ethyl acetate 100a1 was added to the residue, and the mixture was washed with 5% potassium carbonate aqueous solution and diluted hydrochloric acid. After dehydration with magnesium sulfate, the solvent was removed under reduced pressure, and the residue was recrystallized from isopropanol 301111 to obtain the desired exemplary coupler (2).
I got it. Yield 5.5g (60%).

The structure of exemplary coupler (2) was confirmed by NMR, IRl and mass spectroscopy.

Exemplary couplers other than Exemplary coupler (2) were also synthesized according to the above synthesis examples, starting from their respective corresponding raw materials.

The yellow couplers of the present invention can be used alone or in combination of two or more, and can also be used in combination with any known pivaloylacetanilide-based or benzoylacetanilide-based yellow couplers.

In order to incorporate the yellow coupler of the present invention into a silver halide photographic emulsion of a color photographic light-sensitive material, for example, ethyl acetate optionally containing a high boiling point organic solvent having a boiling point of 175° C. such as tricresyl phosphate or dibutyl phthalate; One of the low-boiling organic solvents conventionally used in preparing coupler dispersions, such as methanol, acetone, chloroform, methyl chloride or butyl propionate.
After dissolving the seed or two or more seeds alone or in combination, mixing with an aqueous gelatin solution containing a surfactant, and then emulsifying and dispersing this mixture with a high-speed rotating mixer or colloid mill, the resulting emulsified dispersion The solution is directly added to a silver halide photographic emulsion and then applied to a support and dried, or after the emulsion dispersion is set,
After cutting the material into pieces and removing the low-boiling organic solvent by washing with water or the like, the resulting material may be added to a silver halide photographic emulsion, which is then applied to a support and dried.

Generally, the yellow coupler of the present invention is preferably added in an amount of 10 to 300 g per mole of silver halide, but this amount may be changed depending on the purpose of application.

The silver halide color photographic light-sensitive material of the present invention may be of any type and use, and examples of the silver halide include silver chloride, silver bromide, silver iodide, silver chlorobromide, and silver iodobromide. Silver, silver chloroiodobromide, etc. are used.

The silver halide color photographic light-sensitive material of the present invention may contain, in addition to the yellow coupler of the present invention, other color couplers for forming a multicolor image.

In the silver halide color photographic material of the present invention,
Color antifoggant, image stabilizer, hardener, plasticizer, polymer latex, formalin scavenger-1 mordant, development accelerator, development retardant, optical brightener, capping agent, solvent,
Antistatic agents, surfactants, etc. can be optionally used.

Incidentally, by incorporating an ultraviolet absorber into the silver halide color photographic light-sensitive material containing the yellow coupler of the present invention, the durability of the yellow image formed on the light-sensitive material can be further improved.

〔Example〕

Next, the present invention will be explained with reference to Examples, but the embodiments of the present invention are of course not limited to these Examples.

Example 1 The yellow couplers of the present invention shown in Table 1 (indicated by the numbers given to the above exemplary couplers) and the Y-
Comparison couplers shown as 1 to Y-3 each 3.0X10-”
dibutyl phthalate corresponding to 1/4 of the weight of each yellow coupler and 1/4 of the yellow coupler.
was added to a mixed solution of phenol compound P-1 corresponding to the weight of 40 ml of ethyl acetate, and then heated to 50° C. to dissolve each coupler.

Each solution prepared in this way was mixed with alkanol B.
(alkylnaphthalene sulfonate, manufactured by DuPont) 10% aqueous solution 10++j! and gelatin 5% aqueous solution 2
By mixing with 00II11 and emulsifying it by passing it through a colloid mill several times, 11 types of dispersion liquids (A) containing each of the above couplers were prepared. ) The turbidity of this dispersion (A) was measured. 1/2 amount of the above dispersion liquid (A) at 40°C.
The turbidity of the dispersion (B) which was kept for 8 hours was measured in the same manner, and the results are shown in Table 1.

Next, these dispersions (A) and (B) were added to 500 ml of gelatin silver chlorobromide emulsion, and coated on polyethylene laminate paper so that the coating amount of silver chlorobromide was 0.25 g/nf. Samples 1 to 8 of the present invention and comparative samples 1 to 3 made of silver halide color photographic light-sensitive materials were prepared by drying.

Next, each of the samples thus obtained was subjected to wedge exposure in a conventional manner, and then the exposure method samples were processed according to the development process and processing solution formulation described below.

[Development processing process] Processing temperature Processing time Color development
Bleach and fix at 38°C for 3 minutes and 30 seconds 33
℃ Wash with water for 1 minute 30 seconds 33℃
Dry for 3 minutes 50-80℃ 2 minutes [Color developer composition] Benzyl alcohol 12mj! Diethylene glycol 10mj! Potassium carbonate 25g Sodium bromide
0.6g anhydrous sodium sulfite
2.0g hydroxylamine sulfate
2.5 g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 4.5 g water is added to 11 and the pH is adjusted to 10.2 with NaOI.

[Bleach-fix solution composition]

Ammonium thiosulfate 120g Sodium metabisulfite 15g Anhydrous sodium sulfite 3g EDTA ferric ammonium salt
Add 65g water to make 11 and make pi 6.7 to 6.8
Prepare to.

The maximum color density of the dye image formed on each sample by the above processing was measured, and the sensitivity of these samples was also measured, and the results are shown in Table 1.

Comparison coupler Y-1 CB! Ph h Comparative coupler Comparative coupler (coupler described in JP-A-55-142340) Phenol compound CaHq<t) From the results shown in Table 1, dispersions (A) and (B)
Regardless of the use of dispersions (A) and (B), the samples of the present invention not only produce a higher maximum color density than the comparative samples, but also exhibit higher sensitivity and maximum color density than those produced using dispersions (A) and (B), respectively. It can be seen that excellent dispersion stability is exhibited not only in the case of color development but also in the coupler dispersion liquid stored over time.

Example 2 Sample 9 of the present invention consisting of a multicolor silver halide photographic light-sensitive material was prepared by sequentially coating each layer having the composition shown above on a paper support laminated with polyethylene on both sides from the support side. Created.

1st layer: Blue-sensitive silver halide emulsion layer Monodisperse emulsion made of silver chloride containing 199.5 mol% or more of AgC... Silver coating amount: 3.2■
/100aaExemplary turnip of the present invention? -(11...
6.8■/100cd dibutyl phthalate...
3.5■/100cj gelatin...
... 13.5■/1 0 0cj 2nd layer:
Middle class HQ-1・・・・・・・・・・・・・・・・・・
0.5■/100c11 dibutyl phthalate...
0.5■/100aJ gelatin...
.... 3rd gelatin layer containing 9.0■/1 0 0cI+1; green-sensitive silver halide emulsion layer AgCj! Monodisperse emulsion consisting of silver chloride containing 99.5 mol% or more... Silver coating amount 2.5 ■
/100cd magenta coupler (M-1) Dibutyl phthalate... Gelatin... 4th layer: Intermediate layer ultraviolet absorber (UV-1) Dibutyl phthalate... HQ-1.・・・・・・・・・・・・・・・・・・ze
La Chin・・・・・・3.5*/1001
00 c, Og/100ad 12.0■/100cj 0.7■/1 6.0■/1 0.5■/1 12.0■/1 Qcj Qd 0CII O〇- Containing gelatin layer 5th layer: Red-sensitive silver halide emulsion layer Monodispersed emulsion consisting of silver chlorobromide containing 80 mol% of AgBr...Silver coating amount: 3.0■/10
'Ocd cyan coupler (C-1) 4.2■/100cd Tricresyl phosphate...3.5■/10
0cj gelatin・・・・・・・・・ 11.
5 ■ / 1 00cj 6th layer: Protective layer gelatin 8
．． Next, in place of the exemplified coupler (1) of the present invention used in the first layer of Sample 9 of the present invention, the couplers of the present invention and comparative couplers shown in Table 2 were used as examples of the present invention, respectively. The only difference from inventive sample 9 was that the same molar amount of the coupler was used, and inventive samples 10 to 12 and comparative samples 4 to
6 were prepared respectively.

The sample thus obtained was subjected to edge exposure in a conventional manner, and then the exposure method sample was processed according to the development process and processing solution formulation described below.

Development process Processing temperature Processing time Color development
Bleach and fix at 35.0±0.3℃ for 45 seconds 35.
0±0.5℃ Stabilized for 45 seconds 30-34℃ 9
Dry for 0 seconds Naturally dry at room temperature (25℃) [Color developer composition] Pure water 800m
j! Trietamethramine 10gN,
N-diethylhydroxylamine 5g Potassium bromide 0.02g Potassium chloride
2g potassium sulfite
0.3g 1-hydroxyethylidene 1,1-diphosphonic acid 1.0g ethylenediaminetetraacetic acid 1.0g catechol-3,
5-disulfonic acid disodium salt 1.0 g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 4.5 g optical brightener (4,4'-diaminostilbendisulfonic acid derivative )
10g potassium carbonate
Add 27g of water to bring the total volume to 11 and adjust the pH to 10.1.
Adjust to 0.

[Bleach-fix solution composition]

Ferric ammonium ethylenediaminetetraacetic acid dihydrate 60g ethylenediaminetetraacetic acid 3g ammonium thiosulfate (
70% aqueous solution) 100+11 Ammonium sulfite (40% aqueous solution) 27.5mm! Add water to bring the pH to 11 and adjust the pH to 11 with potassium carbonate or glacial acetic acid.
Adjust to 6.2.

[Stabilizing liquid composition]

5-chloro-2-methyl-4 isothiazolin-3-one 160 g ethylene glycol 1.0 g 1-hydroxyethylidene-1,1 diphosphonic acid 2.0 g ethylenediaminetetraacetic acid 1.0 g ammonium hydroxide (20% aqueous solution) 3.0 g ammonium sulfate
3.0g optical brightener (4,4'-diaminostilbene diphosphonic acid derivative) 1.5g water was added to bring the volume to 11, and sulfuric acid or potassium hydroxide was added to make pi (7)
．． Adjust to 0.

The maximum color density and fog of the dye image formed on each sample by the above processing were measured, and the sensitivity of these samples was also measured, and the results are shown in Table 2.

(Margin below) Q-1 0 ■ LIV-1 Table 2 *Sensitivity is the sensitivity of comparative sample 4 by 1 Relative to 00 Expressed as sensitivity.

From the results shown in Table 2, the sample of the present invention not only forms a dye image with a higher maximum color density and less fog than the comparative sample, but also exhibits high sensitivity. Therefore, the coupler of the present invention has excellent color-forming properties. You can see that

Example 3 On a triacetyl cellulose film support, each layer having the composition shown below was sequentially formed from the support side to prepare sample 13 of the present invention, which is a multilayer color photosensitive material sample. (The amounts added in silver halide photographic light-sensitive materials are expressed in grams per unit unless otherwise specified. Silver halide and colloidal silver are expressed in terms of silver. The sensitizing dye is silver (expressed in moles per mole) 1st layer; antihalation layer (HC-1) black colloidal silver 0.15 UV absorber (U'tl
-2) 0.20 colored coupler (CC
-1) 0.02 high boiling point solvent (Oil-1)
0.20 high boiling point solvent (Oil-2)
0.02 gelatin 1.
6 Second layer; Intermediate layer (IL-1) Gelatin 1.3 Third layer; Low-sensitivity red malignant emulsion layer (R-L) Silver iodobromide emulsion (Em-1
) 0.4 (Em-2) 0.3 Sensitizing dye (S-1) 3.2 1 mol) 〃 (S-3)0.2X10-' (mol/1 mol of silver) Cyan coupler (C-2) 0.50〃
(C-3) 0.13 colored cyan coupler (CC-1) 0.07 DIR compound (D-1
) 0.006 (D-2)
0.01 high boiling point solvent (Oil-1)
0.55 additive (SC-1)
0.003 gelatin 1.0
4th layer: High sensitivity red-sensitive emulsion 1i (R-H) Silver iodobromide emulsion (Em-3) 0.9 sensitizing dye (S-1)
1.7 x 10 (mol/silver 1 mol) ' (S-2) 1.6X10-' (mol/silver 1 mol) 〃 (S-3) 0. lXl0 (mol/silver 1 mol) Cyan coupler (C-3) 0.23 Colored cyan coupler (CC-1) 0.03 DIR compound (D-2) 0.02 High boiling point solvent (Oil
-1) 0.25 additive (SC-1)
0.003 gelatin
1.0 5th layer; Intermediate layer (IL-2) Gelatin 0.8 6th layer; Low-sensitivity green-sensitive emulsion layer (GL) Silver iodobromide emulsion (Em-1
) 0.6 (Em-2) 0.2 Sensitizing dye (S-4) 6.7 x 10-' (mol/silver 1 mol) Sensitizing dye (S-5) 0.8 x 10-' (mol/l
! 1 mole) Magenta coupler (M-2) 0.17”
(M-3) 0.43 colored magenta coupler (CM-1) 0.10 DIR compound (D-3
) 0.02 high boiling point solvent (Oil-2)
0.70 additive (SC-1)
0.003 gelatin 1
．． 0 7th layer; High-sensitivity green-sensitive emulsion layer (GH) Silver iodobromide emulsion (Em-3) Sensitizing dye (S-6) 1.1X1 0.9 (mol/silver 1 mol) 〃 (S -7) 2.0X10-' (mol/1 mole of silver) (S-8) 0.3X10-' (mol/1 mole of silver) Magenta coupler (M-2) 0.03
(M-3) 0.13 colored magenta coupler (CM-1) DIR compound (D-3) High boiling point solvent (Qil-2) Additive (SC-1) Gelatin 8th layer; Yellow filter layer (YC) Yellow Colloidal silver additive (H3-1) -(H3-2) 〃 (SC-2) High boiling point solvent (Oil-2) Gelatin 9th layer; Low sensitivity blue-sensitive emulsion layer (BL) Silver iodobromide emulsion (Em-1) 〃 (Em-2) Sensitizing dye (S-9) 5.8 X 10-'0.04 0.004 0.35 0, 0 0 3 1.0 0.1 0.07 0 .07 0.12 0.15 1.0 0.25 0.25 (mol/silver 1 mol) Yellow coupler (Exemplary couplers of the present invention α order 1.1 DIR compound (D-1) 0.003
(D-2) High boiling point solvent (Oil-2) Additive (SC-1) Gelatin 10th layer; high-temperature blue-sensitive emulsion layer Silver iodobromide (Em-4) Enhanced dye (S-10) 3. 0X10 (mol/1 mole of silver) 〃 (S-11) 1.2X10-4 (mol/1 mole of silver) Yellow coupler (exemplary coupler of the present invention (to)) 0.3
4 High boiling point solvent (Oil-2) 0.06 Additive (SC-1) 0.002 Gelatin 1.0 11th layer; 1st protective layer (PRO-1) Silver iodobromide (Em-5) Ultraviolet absorption Additive (UV-2) -(UV-3) Additive (H3-1) (B-H) 0, OO6 0,21 0,004 1,3 0,3 0,07 0,1 0,2 0゜5 Additive (H3-2) 0.1 High boiling point solvent (Oil-1) 0.07
(Oil-3) 0.07 gelatin
0.8 12th layer; 2nd protective layer (PRO-2) Alkali-soluble matting agent 0.13 (average particle size 2 μm) polymethyl methacrylate) 0.02 (average particle size 3 μm) Slip agent ( WAX-1) 0.04 Charge control agent (SU-1) 0.004
(SU-2) 0.02 gelatin
In addition to the above composition, each layer contains a coating aid of 5U-45 and a dispersion aid of 5U-3. Hardener H
-1, H-2° Stabilizer 5T-1, Preservative DI-1, Antifoggant AF-1. AF-2. Dye Al-1, Al-2
was added as appropriate.

The emulsions used in the above samples are as follows.

Both are monodisperse emulsions with high internal iodine content.

Em-1: Average Agl content 7.5 mol% Octahedron 0
．． 55 μm (particle size) Em-2: Average Agl content 2.5 mol% Octahedron 0
．． 36 μm (particle size) Em-3: Average Agl content 8.0 mol% Octahedron 0
．． 84 μm (particle size) Em-4: Average AgI content 8.5 mol% Octahedron 1
．． 02 μm (particle size) Em-5: Average Agl content 2.0 mol%, 0.08
μmI Ci! c-1 M-1 D-3 JV-2 V-3 gos S-1 S-2 ((CHz=cH5(hcHz) 5CCHzsOtc
Htc)I z )zNcHzcHzsOJ U Na0)S-CI-COOCHz(CFzCFz) 3
HCHg-COOCHt(ChCh): IHU-2 U-3 (Alkanol ssO3 -Kageji S-6 (C11□)3SO! C-2 CIlkoH Volume I3 Sn i1 I-1 tHs I T-1 l-1 0■ MW: 30,000 F-1 F- 2 τ//: 9,000 Furthermore, in place of the inventive coupler α- used in the 9th layer and the 10th layer of the inventive sample 13, the inventive couplers shown in Table 3 were used in the same molar amount. Replace with
Invention samples 14 to 21 and comparative samples 7 and 8 were prepared, respectively.

Each of the samples thus obtained was subjected to wedge exposure in a conventional manner, and then the samples of the exposure method were processed according to the following development process and processing solution formulation.

Processing process (38℃) Color development 3 minutes 15 seconds Bleaching 6 minutes 30 seconds Washing with water 3 minutes 15 seconds Fixing
Wash with water for 6 minutes and 30 seconds
Stabilized for 3 minutes and 15 seconds
Drying for 1 minute and 30 seconds The composition of the treatment liquid used in each treatment step is as follows.

[Color developer]

4-amino-3-methifre N-ethyl-N-β-hydroxyethylaniline sulfate 4.75 g Anhydrous sodium sulfite 4.25 g Hydroxylamine 1/2 sulfur fa salt 2. Og Anhydrous Potassium Carbonate 37.5 g Sodium Bromide
1.3g nitrilotriacetic acid trisodium salt (l hydrate) 2.5g potassium hydroxide 1.0g Add water and 1! shall be.

[Bleach solution]

Ethylenediaminetetraacetic acid iron (DI) ammonium salt 100 g Ethylenediaminetetraacetic acid diammonium salt 10.0 g Ammonium bromide 150.0 g Glacial acetic acid
Add 10-l water to make 11,
Adjust the pH to 6.0 using aqueous ammonia.

[Fixer]

Ammonium thiosulfate 175.0g Anhydrous sodium sulfite 8.5g Sodium metasulfite 2.3g Add water to make 11, and adjust to pH=6.0 using acetic acid.

[Stabilizing liquid]

Formalin (37% aqueous solution) 1.5-E Conidanx (
(manufactured by Konica Corporation) Add 7.5*J water to make 1.

Comparative coupler Y-4 CIl, Ph Comparative coupler (coupler described in JP-A-55-142340) Table 3 *2 Fog is shown as the difference from the fog value of comparative sample 7.

113 The amount of the coupler of the present invention added is: The amount was set at 172 mol.

From the results shown in Table 3 for the amounts of other samples added, the sample of the present invention not only has a higher maximum color density and forms a dye image with less fog than the comparative sample, but also exhibits high sensitivity. It can be seen that the invention coupler has excellent coloring properties.

〔Effect of the invention〕

As is clear from the above description, according to the present invention,
Excellent color development and high solubility in low boiling point solvents.
A silver halide color photographic light-sensitive material containing a 2-equivalent yellow coupler exhibiting excellent dispersion stability in the solvent is provided.

applicant

Claims (1)

[Scope of Claims] In a silver halide color photographic light-sensitive material having at least one silver halide emulsion layer on a support, at least one of the silver halide emulsion layers has the following general formula [I
A silver halide color photographic light-sensitive material containing a 2-equivalent yellow coupler represented by the following. General formula [I] Y-(J-R_1)_m-O-R_2(O-R_3)_
n-(R_4)_q-X-R_5 (wherein, Y is -(J-
R_1)_m-O-R_2-(O-R_3)_n-(R
_4) Represents a 2-equivalent yellow coupler residue containing a group represented by _q-X-R_5. R_1, R_2, R_
3 and R_4 each represent an alkylene group or an arylene group. R_5 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group. m and q represent 0 or 1, n
represents an integer from 2 to 10. J and X represent a divalent linking group connected via a heteroatom. )